The Pittsburgh Pirates have spent the past decade constructing what is now a perennial contender. Andrew McCutchen, Starling Marte, Gregory Polanco, Neil Walker, Josh Harrison, Jordy Mercer, Francisco Cervelli, and Jung Ho Kang are under wraps through at least 2016, with McCutchen, Marte, Polanco, Harrison, and Mercer locked in through 2018. Ace starter Gerrit Cole is under team control through 2019. Strikeout extraordinaire Francisco Liriano is signed through 2017. Top pitching prospect Tyler Glasnow, who averaged over 11 strikeouts per nine innings at High-A, Double-A, and Triple-A in 2015, is a near-lock to be installed in the rotation next season. Ace relievers Mark Melancon and Tony Watson are due for big arbitration raises, but they’ll be around in 2016.

The organization also sports a savvy and well-rounded manager in Clint Hurdle and a general manager in Neal Huntington who has a knack for finding undervalued or discarded assets (Cervelli, Kang, Liriano, A.J. Burnett, Marlon Byrd, J.A. Happ, Russell Martin) and brilliantly managing the Pittsburgh’s modest $90 million payroll (no Pirate is scheduled to make more than $13.6 million in 2016, and no Pirate that began 2015 with the club had a salary over $11.6 million.)

The Pirates, who are playing October baseball for the third straight season, aren’t going to stop winning big in the regular season anytime soon—which is actually saying quite a lot, because it was just three years ago that Pittsburgh completed its 20th consecutive season sans a playoff appearance or a winning record. The last time the Pirates reached the postseason in three successive years was from 1990-92, and during that three-year run, Barry Bonds captured his first two Most Valuable Player awards, Doug Drabek won a Cy Young, and manager Jim Leyland presided over a club that averaged 96.3 wins in the regular season. Pittsburgh was a regular-season juggernaut.

The record books indicate that the Pirates advanced to the National League Championship Series each year from 1990-92, but the club didn’t need to win a playoff series to reach the NLCS, as the entire postseason consisted of just four teams during that era. Still, Pittsburgh received a heavy dose of heartbreak in each NLCS appearance, losing to the Reds in six games in 1990 (Glenn Braggs happened) and falling to the Braves in a deciding Game 7 in both 1991 (John Smoltz and Steve Avery happened) and 1992 (Sid Bream happened). The Pirates’ present core has not endured that level of anguish, but there have been October pitfalls over the past two years. In 2013, the Pirates won 94 games and went ahead of the Cardinals two games to one in a NLDS matchup, only to see St. Louis rally for a 3-2 series victory. Last season, the Giants blanked the 88-win Pirates 8-0 in the Wild Card Game.

Despite being set up for additional 90-win seasons for years to come, there’s no better time than the present for the Pirates to win a playoff series and position themselves for a world championship. As the 1990-92 Pirates can attest, potential can only take a club so far, and there’s no telling when the roof can cave in on an organization’s promising future.

Season Wins ERA/NL rank out of 14 teams wRC+/NL rank out of 14 teams
1990-92 96.3 3.40/1st 104/1st
1993 75 4.77/13th 95/6th

Following the 1992 season, Bonds and Drabek left as free agents (after Bobby Bonilla departed after the 1991 season). The Pirates retained a handful of key position players in Andy Van Slyke, Jay Bell, Orlando Merced, and Don Slaught to complement Randy Tomlin, Zane Smith, and Bob Walk, a trio of hurlers who started the majority of the games for the Pirates (outside of Drabek) for the Pirates from 1990-92. Tomlin, Smith, and Walk combined to start 64 games for the 1993 Pirates, but all three regressed from their 1990-92 form.

The Pirates need not look far to realize how fleeting postseason success can be, a hard truth known by their NL Central rivals, the Cincinnati Reds.

The Reds prevailed 91 times in 2010 to win their first division title in 15 years, then won 97 games two years later to clear the second-place Cardinals by nine games. In 2013, the Reds won 90 games and qualified for the NL Wild Card Game. Playoff success for Cincinnati proved to be elusive, though. The Reds were swept in three games by the Phillies in 2010, lost three straight home games to blow a 2-0 division series advantage to the eventual World Series champion Giants in 2012, and were shamed 6-2 by the host Pirates in the 2013 NL Wild Card Game. Because they’ve been responsible financially, the Pirates are in better shape to last longer than the Reds, who handed long, lavish extensions totalling a combined $429 million to Homer Bailey, Brandon Phillips, and Joey Votto from 2012-14. After losing 86 times in 2014, the Reds dropped 98 games this year, the franchise’s worst season since 1982.

The point is, one can never be sure when disaster or heartbreak will strike. The Pirates already suffered one serious blow when Kang, the club’s most productive hitter during the second half of the season and one of the top batters in the NL post-All-Star Break, was lost for the season after breaking his left leg and tearing the MCL in his left knee on Sept 17.

The Pirates shouldn’t be intimidated by any other NL squad. The Cardinals won 100 games, but their gaudy record belies a middling offense, and Yadier Molina’s status remains up in the air for the NLDS. Though the Cubs have a manager in Joe Maddon who is fluent in the roller-coaster ride that is playoff baseball, Chicago’s regulars possess either very little or no postseason experience. The Dodgers and Mets are good teams, but there’s a reason why the Pirates’ run differential far exceeded both outfits from April through early October.

For the Pirates’ sake, I hope tonight’s Wild Card Game is the launching point of the deep October run their well-constructed roster deserves.